Bradsher反应

分子内的Bradsher环化反应是指在酸催化下邻酰基二芳基甲烷进行芳香环化脱氢生成蒽的反应。

反应机理：

反应实例

另外Bradsher环加成反应是指乙烯基醚或乙烯基硫醚对吡啶盐进行Diels–Alder加成的反应。

参考文献

1. (a) Bradsher, C. K. J. Am. Chem. Soc. 1940, 62, 486–488. Charles K. Bradsher was born in Petersburg, VA in 1912. After his Ph.D. under Louis F. Fieser at Harvard and postdoctoral training with R. C. Fuson, he became a professor at Duke University. (b)Bradsher, C. K.; Smith, E. S. J. Am. Chem. Soc. 1943, 65, 451–452. (c) Bradsher, C.K.; Vingiello, F. A. J. Org. Chem. 1948, 13, 786–789. (d) Bradsher, C. K.; Sinclair, E.F. J. Org. Chem. 1957, 22, 79–81.

2. Vingiello, F. A.; Spangler, M. O. L.; Bondurant, J. E. J. Org. Chem. 1960, 25, 2091–2094.

3. Brice, L. K.; Katstra, R. D. J. Am. Chem. Soc. 1960, 82, 2669–2670.

4. Saraf, S. D.; Vingiello, F. A. Synthesis 1970, 655.

5. Ahmed, M.; Ashby, J.; Meth-Cohn, O. J. Chem. Soc., Chem. Commun. 1970, 1094–1095.

6. Ashby, J.; Ayad, M.; Meth-Cohn, O. J. Chem. Soc., Perkin Trans. 1 1974, 1744–1747.

7. Bradsher, C. K. Chem. Rev. 1987, 87, 1277–1297. (Review).

8. Nicolas, T. E.; Franck, R. W. J. Org. Chem. 1995, 60, 6904–6911.

9. Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 39, 837–840.

10. Urban, D.; Duval, E.; Langlois, Y. Tetrahedron Lett. 2000, 41, 9251–9256.

11. Soll, C. E.; Franck, R. W. Heterocycles 2006, 70, 531–540.

13. Mondal, M.; Kerrigan, N. J. Bradsher Reaction, In Name Reactions for Carbocyclic Ring Formations, Li, J. J., Ed.; Wiley: Hoboken, NJ, 2010, pp 251-􀀐266. (Review).

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Bradsher reaction，page 77-78.